(1R,2R,3S,4S,2'S,3'S,5'S)-1-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2,4-dimethyl-1-triethylsilanyloxyhex-5-en-3-ol

Base Information

Chemical Name:(1R,2R,3S,4S,2'S,3'S,5'S)-1-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2,4-dimethyl-1-triethylsilanyloxyhex-5-en-3-ol
CAS No.:845536-49-4
Molecular Formula:C₄₁H₆₈O₈Si
Molecular Weight:717.072
Hs Code.:

(1R,2R,3S,4S,2'S,3'S,5'S)-1-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2,4-dimethyl-1-triethylsilanyloxyhex-5-en-3-ol

Synonyms:(1R,2R,3S,4S,2'S,3'S,5'S)-1-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2,4-dimethyl-1-triethylsilanyloxyhex-5-en-3-ol

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Chemical Property of (1R,2R,3S,4S,2'S,3'S,5'S)-1-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2,4-dimethyl-1-triethylsilanyloxyhex-5-en-3-ol

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Technology Process of (1R,2R,3S,4S,2'S,3'S,5'S)-1-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2,4-dimethyl-1-triethylsilanyloxyhex-5-en-3-ol

There total 5 articles about (1R,2R,3S,4S,2'S,3'S,5'S)-1-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2,4-dimethyl-1-triethylsilanyloxyhex-5-en-3-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 845536-62-1
(2S,3R,2'S,3'S,5'S)-3-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2-methyl-3-triethylsilanyloxypropanal

: 624-64-6
trans-2-Butene

: 845536-49-4
(1R,2R,3S,4S,2'S,3'S,5'S)-1-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2,4-dimethyl-1-triethylsilanyloxyhex-5-en-3-ol

Guidance literature:: trans-2-Butene; With (-)-B-methoxydiisopinocamphenylborane; n-butyllithium; potassium tert-butylate; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; at -78 - -45 ℃; for 1h;

(2S,3R,2'S,3'S,5'S)-3-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2-methyl-3-triethylsilanyloxypropanal; In tetrahydrofuran; at -78 ℃; for 4h;

With sodium hydroxide; dihydrogen peroxide; In water; at 20 ℃; for 12h;
DOI:10.1021/ol047779s

Reference yield:

: 845536-46-1
(2S,3R,2'S,3'S,5'S)-3-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2-methyl-3-triethylsilanyloxypropan-1-ol

: 845536-49-4
(1R,2R,3S,4S,2'S,3'S,5'S)-1-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2,4-dimethyl-1-triethylsilanyloxyhex-5-en-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrapropylammonium peruthenate; 4-methylmorpholine-N-oxide / CH₂Cl₂ / 0.67 h / 20 °C

2.1: (-)-B-methoxydiisopinocampheylborane; n-BuLi; tert-BuOK / BF₃*Et₂O / tetrahydrofuran; diethyl ether / 1 h / -78 - -45 °C

2.2: tetrahydrofuran / 4 h / -78 °C

2.3: 18.8 mg / NaOH; H₂O₂ / H₂O / 12 h / 20 °C

With (-)-B-methoxydiisopinocamphenylborane; n-butyllithium; tetrapropylammonium perruthennate; potassium tert-butylate; 4-methylmorpholine N-oxide; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; dichloromethane; 2.2: Brown asymmetric crotylation;
DOI:10.1021/ol047779s

Reference yield:

: 2'-[benzyl-(2,4,6-trimethylbenzenesulfonyl)amino]-1'-phenylpropyl (2S,3RS,1'S,2'R,2''S,3''S,5''S)-3-[2-(6''-benzyloxy-2''-methoxymethoxy-3'',5''-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-3-hydroxy-2-methylpropionate

: 845536-49-4
(1R,2R,3S,4S,2'S,3'S,5'S)-1-[2-(6'-benzyloxy-2'-methoxymethoxy-3',5'-dimethylhexyl)-3,5,6-trimethoxy-4-methylphenyl]-2,4-dimethyl-1-triethylsilanyloxyhex-5-en-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 89 percent / DIBALH / toluene / 1 h / -78 °C

3.1: tetrapropylammonium peruthenate; 4-methylmorpholine-N-oxide / CH₂Cl₂ / 0.67 h / 20 °C

4.1: (-)-B-methoxydiisopinocampheylborane; n-BuLi; tert-BuOK / BF₃*Et₂O / tetrahydrofuran; diethyl ether / 1 h / -78 - -45 °C

4.2: tetrahydrofuran / 4 h / -78 °C

4.3: 18.8 mg / NaOH; H₂O₂ / H₂O / 12 h / 20 °C

With (-)-B-methoxydiisopinocamphenylborane; n-butyllithium; tetrapropylammonium perruthennate; potassium tert-butylate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 4.2: Brown asymmetric crotylation;
DOI:10.1021/ol047779s